Chimney Crocket on Mission Roof - Flashing

I apologize if this has been covered before. I searched the forums and could not find an answer specific to my question.

I have a clay tile roof, Mission Style, with a chimney. There is a cricket on the high side of the chimney. I've lived in this house about 12 years. A couple of years ago I noticed the soffit and fascia rotted on each side of my chimney. I attempted to replace each and also replaced some decking, rafters and the tar paper. I replaced the tiles and flashing as it was although the I had to bend up the counter. It would not bend back down so I rigged it best I could. Keep in mind that my finances are such that I could afford to hire someone to do it professionally. Flash forward to the present. When it rains, I can see the rain trickling down the sides of chimney. It also runs into the soffit. Since I had replaced decking, rafters and tar paper I figured I had some time to get this done.

I'm thinking one of the issues is that leaves and sticks get caught underneath the tiles from the exposed cricket. Another issue after reading up is that the base flashing is a simple L-shape instead of a pan or channel flashing. I can fix the base flashing. I order a brake bender to fashion new flashing. I realize that I also have to redo the counter flashing but my biggest concern is the cricket. Any suggestions on how I can keep the leaves and such from getting under the tiles?